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1st February 2012 @ 23:24
Used crude in PMY 34-1.


Boc-deprotection of PMY 29-2-A in THF using TFA.

Reaction Scheme

Reaction Start time: 0930 02/02/12
PMY 29-2-A was dissolved in THF (5 mL). Yellow solution. TFA (0.5 mL) was added dropwise. Solution turns red during addition. After 2.5 hours, no reaction by TLC. HCl (4M in dioxane, 0.5 mL, 2 mmol) was added. After a further hour, a slightly yellow precipitate had formed. Reaction not complete after 5 hours. Further HCl (4M in dioxane, 2.0 mL, 8 mmol) was added. Reaction not complete after a total of 9 hours. After overnight stirring, the reaction is complete by TLC. Reaction concentrated under a stream of nitrogen to a yellow solid and to be used crude in experiment PMY 34-1.

TLC (10% MeOH/vanillin) visualised with UV and vanillin:
TLC 3.5 hours
TLC 2.5 hours

See also:
Deprotection of Boc-Gly-4-aminoantipyrine (PMY 30-2)
Deprotection of Boc-Gly-4-aminoantipyrine (PMY 30-1)

Risk and Hazard Assessment:
Linked Entries
Attached Files
TLC 2.5 hours
TLC 3.5 hours